


Unexpected Love

by Lboogie0711



Category: Gilmore Girls
Genre: M/M
Language: English
Status: In-Progress
Published: 2019-12-25
Updated: 2021-01-22
Packaged: 2021-02-26 03:01:07
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 13
Words: 8,751
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21962515
Author URL: https://archiveofourown.org/users/Lboogie0711/pseuds/Lboogie0711
Summary: Dean's life is turned upside down until Jess changes everything
Relationships: Dean Forester/Jess Mariano
Comments: 1
Kudos: 20





	1. Revelations

**Author's Note:**

> First time writing a Gilmore girls fan fiction.

Dean Forester had lived his life happily he was married and had kids. Rory was a memory of his first relationship. Or so he thought, Dean came home to find his wife’s things packed up. “What’s going on?” Dean asked. “I can’t do this anymore” his wife said packing her suitcase. “What do you mean?” Dean asked. “This, this life were living” his wife said. “What is wrong, we can fix this” Dean said trying to stop his wife from leaving. “It’s too late, I’m sorry but I need a break, the kids can stay with me for a while at my parent’s place and i’ll let them stay at your parent’s house” his wife said. “You can’t be serious, for how long!” Dean yelled. “I don’t know as long as I need” his wife said crying. Dean’s kids didn’t want to leave so dean dropped them off at his parent’s house. “This won’t be forever, I’ll try to fix things with mom so that we can be a family again” Dean said trying to be strong. “Dad… mom’s been with someone else” Dean’s son said. Dean left the house, angry, betrayed, and most of all heartbroken. 

Dean sat in a bar near Stars Hollow. Drowning his sorrows in alcohol helped him until after his third drink, he started to feel tipsy. Dean started to leave when he nearly fell until someone caught him. The mysterious person helped Dean to his car and drove him home. The person lead Dean upstairs to his bedroom and laid him on his bed. They took off his shoes and were about to leave until Dean grabbed their hand. “Can you stay” Dean asked. “No you need to rest” said the voice. Dean grabbed the person and them pulled down onto the bed. “I don’t want to be alone” Dean said in a drunken haze “Guess I’m staying then” said the voice with a sigh Dean kissed the mysterious person and started to undress but felt tried and fell asleep on top of the mysterious person.

The next morning, Dean woke up and had a massive headache. He turned over to see Jess Mariano sleeping next to him. Dean leaped out of bed in shock. How and why was Jess in his house. Jess yawned then woke up. "Morning how are you" Jess asked still half asleep " I've been better. Quick question, how are you in my bedroom" Dean said. “Well you were flat out drunk last night and I happened to be passing through Stars Hollow so I drove you home from the bar and put you to bed. You asked me to stay the night and when I tried to leave, you kissed me and then fell asleep" Jess said. "Oh god, I'm sorry. My wife had left and I dropped off my kids at my parent's house and I didn't want to be alone" Dean said "Don't be sorry, you had every right to be upset and I'm just glad that I was here to help you" Jess said. “Thank you for everything, by the way. I don't know what I would have done" Dean said. Jess got out of bed and went to the bathroom. Dean couldn't believe how good Jess looked. His black hair and beard looked so good and he slept adorably. Wait what was he thinking.... This was Jess. The guy who he had fought for Rory's heart and in the end both lost. There was no way Dean could be falling for Jess. 

Jess put on his clothes and Dean went downstairs to make them breakfast. Jess came downstairs as soon as Dean was finished making the food. "Thanks Dean for the breakfast, but you didn't have too" Jess said. "I kind of did. Besides it was no trouble at all. Listen I got to pick up my kids later, but I got called in for later shift at work. Think you could pick them for me?" Dean asked “Sure no problem" Jess said


	2. After school fun

**Summary for the Chapter:**

> Jess takes dean's kids to Luke's diner and then makes dinner with the kids for Dean

Jess went to the school where dean’s kids were attending and picked up the kids. “Hi Mr Mariano what are you doing here?” Dean’s daughter asked. “I am here to pick you guys up while your dad is at work” Jess said as he opened the door for the kids. “I thought our mom was gonna pick us up” Dean’s son said. “Well she was busy… with other things” Jess said trying not to state the obvious situation. “Yeah busy with her new boyfriend. How could she do that” Dean’s daughter asked. “I’m not sure why she did what she did either. What do you say we head to Luke’s for an after school snack and then head home?” Jess asked. “Yeah!” Dean’s kids yelled with excitement. Jess drove the kids to Luke’s for some milkshakes. Jess got himself a burger and fries. “Hey Jess” Luke said. “Hey uncle Luke” Jess said. “What are you doing with Dean’s kids” Luke asked. “I’m babysitting while he’s at work” Jess said. “How did you get roped into this?” Luke asked. “I offered to help” Jess said. “Well I think that was a nice of you, hey i’m having dinner with Lorelai tonight if you want to stop by” Luke said. “Thanks but I’ll probably be watching the kids for the rest of the day” Jess said as he and Dean’s kids were leaving the diner. 

Jess and Dean’s kids went inside Dean’s house and got settled in, the kids went off to do their homework while Jess decided to prepare dinner. “So what would you guys like for dinner, anything you want” Jess said. “I think that you should make something chicken” Dean’s son said. “Yeah that would be good” Dean’s daughter said. “Sure I’ll start prepping the food and then when you guys are finished with your homework, you can help me” Jess said. Jess washed his hands then began washing the chicken thoroughly, mixing the lemon juice, oil, and melted butter then rubbed the chicken. After that he seasoned the chicken and put the chicken in the oven. The kids came into the kitchen to help Jess cook rice and vegetables. Once Dean got home, the kids were setting the table. “Hey kids, what’s going on?” Dean asked. “We helped Jess make dinner” Dean’s son said. “Really, Jess made us dinner” Dean said “Yeah he thought it would be nice to do for us” dean’s daughter said. “Well thank you Jess for making dinner” Dean said. “Your welcome. And let’s dig in” Jess said. They sat around the table and ate the chicken, rice, and broccoli that Jess and the kids made. 

After dinner the kids got ready for bed while dean and Jess talked in the kitchen. “Thank you again for watching them and making dinner” Dean said. “No problem” Jess said. “So i talked to my wife today and she stills wants to take a break" Dean said. “Dean i’m sorry, if there’s anyway I can help i’ll do it” Jess said “It’s all right, I have should seen the signs coming from a mile away” Dean said staring off into the distance. “Hey why don’t you get some rest and tomorrow you can spend the day with your kids” Jess said. “Yeah that sounds nice, you could come too if you want” Dean said. “Yeah, yeah sure I’ll come with” Jess said. "Great see you tomorrow" Dean asked. Dean went upstairs to say goodnight to his kids. "Dad do you like Jess?" Dean's daughter asked "What do you mean honey?" Dean said "Well he's really sweet, kind, and makes you smile a lot" Dean's daughter said. "Yeah and he cooks, way better than mom ever did" Dean's son said. Dean thought about it, did he like Jess.

The next day Jess met Dean and his kids bright and early at the playground. Dean and Jess sat and watched on a bench while they talked. "So we should talk" Dean said. "Sure what's up?" Jess asked. "Well my kids think that I like you" Dean said. "Do you?" Jess asked. "I don't know yet" Dean said "Whatever you decide I'll be fine with it" Jess said. After an hour at the playground, Dean and Jess took the kids home. Dean's wife was there at the house. "I'll take the kids in and let you guys talk" Jess said. Dean and his wife went into the backyard. "So why are you here?" Dean asked. "To get the rest of my things and to give you these" Dean's wife said as she handed him divorce papers. "Are you kidding me?!" Dean yelled. "Dean please, I'm sorry but I want out of this marriage" Dean's wife said. "Oh yeah sure so you can go be with your new boyfriend" Dean said angry walking away from his wife. "How do you know about that" Dean wife's asked. "The kids told me" Dean said. "I'm sorry you were always working and I was lonely" Dean's wife said trying to talk with him "So you talk to me but you don't cheat on me!" Dean yelled. "Look I don't want to do this here, and I don't want to go to court either" Dean's wife said

After his wife left, Dean started to drink as Jess came downstairs. "Hey so I finally put the kids down for a nap" Jess said. "Great thanks for doing that" Dean said drunk. "Dean really" Jess said "What?" Dean asked. "Your drinking what's wrong" Jess said "Let's see my wife wants a divorce and she'll probably take my kids away" Dean said "Do you want to talk" Jess asked. "Yeah. I just- I don't know where I went wrong, I thought I finally found the one, but she wasn't" Dean said. "You didn't do anything wrong, she just couldn't see how much you loved and cared for her" Jess said hugging Dean. Dean stared at Jess for a minute, wow he looked great, yet Dean couldn't tell if this was the alcohol or his subconscious talking.


	3. The Annoucement

**Summary for the Chapter:**

> Dean and his wife sit their kids down to discuss about their divorce

Dean slowly pulled Jess toward him and kissed him but Jess stopped him.

“Uh maybe I should get going” Jess said. “You don’t have to, you could stay” Dean said “I know but I think it would best if I did” Jess said

Jess left the house and drove away. Dean finished off what was left of the beer and went to bed. It would have been better if Jess had stayed and Dean would have been able to get some sleep. The next morning Dean was a mess, but he couldn’t let his kids know so he tried to make them breakfast. Dean’s kids later came downstairs. 

“Morning dad” his daughter said “Hey dad are you OK?” dean’s son asked. “Yeah bud why” Dean said “Because you look tired, did you sleep” Dean’s daughter asked “Yes well I tried too but couldn’t” Dean said. “Is it because uncle Jess wasn’t here?” his daughter said. “No… wait uncle Jess” Dean said “Yeah uncle Jess, he’s kind of like an uncle” his son said. “Uh OK, but no that wasn’t the reason” Dean said even though he knew it was. “It was so the reason” his daughter whispered. “Just be ready before Jess gets here” Dean said.

Jess arrived right on time while the kids were putting on their backpacks. “Hey guys ready for school?” Jess asked “Yeah!” the kids said ‘All right then you guys go get in the car and I’ll be there in a sec” Jess said. “Hey so how did you sleep” Jess asked Dean once the kids left. “Why does everyone care if I sleep or not?” Dean said “Because we all care about you” Jess said “Well I didn’t” Dean said “Dean why don’t do you take a half day at work to rest and I’ll pick up the kids today for you” Jess said. “Thanks Jess I appreciate it” Dean said as he went off to work. 

Dean managed to sleep and dreamed of his so called happy life. He and his kids were playing in the backyard when Jess came. The kids ran toward him and hugged, then Dean went to Jess and kissed him. Suddenly dean woke up to the sound of the door opening, his kids and Jess were back home. 

“Dad!” the kids said as they ran to him and hugged each other. “Oh! Hey guys how was school?” Dean asked “Good, we learned about maps and how to know our address if we ever get lost” his kids said. “That is so nice” Dean said “Yeah and then uncle Jess took us to Luke’s. “Oh did he now?” Dean said looking at Jess. “Yeah I figured they could see Luke and Loreali before coming home” Jess said. “Thank you for picking them up” Dean said “Your welcome” Jess said. “Hey kids, mom said that she was coming over to talk to you” Dean said. “Oh OK” his son said “Do you want to me to stay with the kids while you and your wife talk?” Jess asked. "No were gonna tell about the divorce” Dean said “Hey i’m here for guys see you later” Jess said as he left. 

Dean’s wife arrived shortly after. “Hi” she said “Hi come on in” Dean said “Kids come down here please” Dean said. The kids came downstairs and sat on the couch. “What is it dad” his daughter asked. “You may have noticed that mom and I have gone through a… rough time in our marriage” Dean said. “And we want you to know that none of this is your fault” his wife said. “Mom and I have decided to… get a divorce” Dean said trying not to seem hurt. “Please don’t be upset with us” his wife said. “The only person we should be upset with is you Mom” his son said “Yeah you hurt dad and that wasn’t nice” “I know I know it was wrong and I am so sorry for everything” Dean’s wife said “If your sorry then why can’t you get back together” his son asked. "Because I don't want too" his wife said. "Why not?!" his son yelled. "It's because of her new boyfriend" his daughter said "Honey, I'm sorry" his wife said. "Kids please let us continue" Dean said trying to calm the kids down. 

The kids settled down. "So what happens now?" his son asked. "Well we would have you guys decide on who you want to stay with" Dean said. "I'm staying with Dad" his son said "I'm staying with dad too" his daughter said. "Kids.... don't either of you want to stay with me" his wife said "No I don't" Dean's daughter said "I don't want to either" Dean's son said. "All right well uh- excuse me" his wife said leaving the room. Dean's kids ran outside. "Kids wait come back!" Dean said 

Dean went to go check on his wife. "Uh you all right" Dean asked. "No I'll be fine. I'm gonna go" his wife said still crying as she left the house. After she left, Dean called Jess. "Jess it's me, my kids ran off somewhere can you help me find them" Dean said "Dean there with me in the park" Jess said "Stay where you are I'll be right there" Dean said as he drove to the park.


	4. Sleepover

**Summary for the Chapter:**

> Jess plans a movie night for Dean and his kids

Dean made it to the park and looked for Jess and his kids. Dean found them sitting on a bench. “Guys there you are. You had me worried sick” Dean said. “Were sorry dad” his son said. “Why did you guys run away?” Dean asked “We didn’t want to have to choose between you and mom, because we knew she’d be hurt” his daughter said. “Kids I know your upset but you shouldn’t have run away like that” Dean said. 

“Your dad is right. This is a terrible situation to be placed in right now but you cannot not let anger take over your emotions” Jess said hugging the kids. “Kids why don’t we go back to the house and talk this over” Dean said. “OK” said the kids. “Jess thanks for watching them and keeping them with you” Dean said. “No worries, just be there for them” Jess said taking off on his motorcycle. Dean was shocked, Jess had a motorcycle. 

Dean took the kids back home and spent time with them. They watched movies, made cookies, and ice cream sundaes. Once the kids were tired, Dean put them to bed. Jess came by a little later to check on everyone. 

“Everything good?” Jess asked. “Yeah were fine, thanks for coming by” Dean said. “Dean if you want me to stay with you and the kids I will” Jess asked. “I think the kids would be really happy if you did” Dean said. Jess chuckled “I’ll stay”. Dean smiled, Jess’s laugh was adorable. 

The kids were ecstatic about Jess coming over tomorrow and having a movie night. That night Jess brought pizza over for the kids. They all gathered around the couch and watched movies on netflix. Dean was happy that his kids were happy and he had Jess to thank for that. Dean knew that his kids were getting tired so he paused the movie. 

“OK kids time for bed” Dean said. “But were not tired” Dean’s son said. “Yeah we can stay up late please dad” Dean’s daughter asked. “No your dad’s right you guys should get some sleep” Jess said. The kids sighed and went up to bed. 

Dean and Jess were getting tired themselves so Dean thought that Jess could stay the night. “I think I will stay the night” Jess said. Dean and Jess went upstairs to Dean’s bedroom. Jess didn’t have a shirt to wear so Dean gave him one of his. Dean chuckled. “What’s so funny?” Jess asked. “My shirt is too big for you” Dean said laughing. “Ha ha very funny. Just go to bed” Jess said annoyed. 

Dean and Jess laid in bed together and Dean looked Jess while he was sleeping. He thought about cuddling with Jess, but was nervous about waking him. Dean decided to take a chance and cuddled Jess. Jess woke up startled and said “Uh dean what are you doing?” Jess asked “Cuddling you” he said. “Thanks I needed that” Jess said. Then Dean took a chance and kissed Jess again.


	5. Date Night

**Summary for the Chapter:**

> Dean and Jess go out on a date

Dean made out with Jess and started to undress. Jess wasn’t sure if they should but Dean really wanted too. “Just try to be quiet as possible” Dean said. They continued to make out and tried not to wake the kids all through the night.  
The next morning Jess was still sleeping, which is what Dean told the kids. Dean had taken the day off to stay with home.

“Hey feeling better” Dean said “No” Jess said still laying on his stomach. Dean tried not to laugh because he knew he was at fault. “Well the kids are with my parents today. We have the whole day to ourselves” Dean said. Jess turned and laid on one side. “Would you say that were dating or lovers?” Jess asked. Dean froze for a second. He hadn’t thought about their relationship status. “Uh I don’t know I mean you come over a lot, you help with the kids, make dinner, etc” Dean said. “I know that, but do you think of me as more than just a friend” Jess asked. “Sometimes but I’m not sure” Dean said. “Would a date change your mind?” Jess said. “Yes it would” Dean said

Dean had no idea where Jess was taking him. Jess would be arriving any minute and he was anxious to find out what the date would be. Jess texted him that he was outside. “Hey ready our date?” Jess said. “Uh yeah… but are we really taking your motorcycle” Dean asked. “Yes and don’t worry I have an extra helmet” Jess said. 

Dean sat behind Jess and held on tight as Jess sped through the streets of Stars Hollow. Jess made a stop near a beach then he made Dean close his eyes. When he opened them, Dean saw a blanket, plates, and a picnic basket. “Wow, I can’t believe you did all this” Dean said. “What can I say, I’m a romantic” Jess said. “Usually I would plan something like this for-” Dean said. Before Dean could finish his sentence, Jess feed him a piece of steak. “No more talking about her” Jess said

Dean loved the steak that Jess had made but the desert was even better. Jess brought a molten chocolate lava cake which was heavenly. After their date on the beach, Jess and Dean went back to Dean’s house. “You know this date was nice” Dean said “I’m glad you enjoyed it” Jess said “Wanna stay the night” Dean asked “Sure” Jess said

Jess went upstairs to take a shower. Jess was rinsing his hair when Dean walked into the bathroom. He was getting for bed and took peeks at Jess in the shower. He figured that Jess wouldn’t notice. “Wanna come in” Jess said. “No I’m good” Dean said teasing him. Once Jess was out of the shower, he went to bed with Dean. 

The next morning Dean went to go get the kids from his parent’s house. “Hello Dean how are you” his mom asked. “I’m good mom thanks for asking” Dean said. “Are you sure, I know how hard it’s been since-” his mom said. “Mom please don’t bring this up especially in front of my kids” Dean said. “Well I’m sorry. I’m your mother I have a right to know everything that happens to you. By the way are you seeing anybody" Dean's mom said. "Mom" Dean said getting annoyed. "All right all right I was just wondering" Dean's mom said. 

Dean picked up the kids and went back home. When they walked in the house, Jess was in the kitchen. "Uncle Jess!" the kids yelled. "Hey guys how was it at grandma's?" Jess asked. "We had so much fun, Grandma baked cakes and pies and we got to take some home with us"  
Dean's daughter said. "She also wants to know who your dating, dad" Dean's son said. "Of course she did" Dean said. "Are you going to tell about uncle Jess" Dean's son asked. "Uh I don't know" Dean said. Dean didn't know it yet but this would cause a problem with his relationship


	6. The Fight and The Talk

**Summary for the Chapter:**

> Dean and Jess get into an argument over their relationship and Dean talks with an old friend.

A few months into their relationship, Dean noticed a change in Jess. He couldn’t put his finger on it, but he knew that Jess was upset about something. Dean decided to talk with Jess about what was wrong. “Hey is everything ok?” he asked. “No everything’s fine, why?” Jess asked. “You just seem kinda distant lately” Dean said. “Dean nothing is wrong” Jess said. Dean knew that Jess wasn’t telling the truth, because Jess didn’t want to start a fight between the two. After they went upstairs, Dean couldn’t let this go and talked to Jess. “Look if I've done something, i’m sorry” Dean said “Dean I said drop it all right” Jess said not wanting to argue. “No whatever it is, you can tell me” Dean said. “Fine you wanna know what you did, it’s what you haven’t done” Jess said angry. “What are you talking about?” Dean said confused. “Since we’ve been together, you haven’t told anyone about us, not your parents, not your soon to be ex wife, not anyone” Jess said. “That’s because I don’t want anyone making a big deal out of this” Dean said. “A big deal- Dean I don’t want to feel like we have to hide your relationship from anyone or anybody in Stars Hollow. Your so concerned with how other people think, that you don’t even think about yourself or us” Jess said hurt. “That is not true. I never wanted to make you feel any less important” Dean said trying not to yell. “But you did. I feel like I’m not there for you in some way and I do not want to feel this way ever” Jess said. “Jess-” Dean said trying to comfort him. “No I didn’t even want to bring this up since your divorce will be finalized soon” Jess said moving away from Dean. “I’m gonna go pick your kids, i’ll see you later” Jess said as he left the room. 

Dean stood in his bedroom in silence, he was so angry that he went for a walk to cool down. He ended up in the town square of Stars Hollow near the gazebo. “Dean?” a voice said that Dean knew from a mile away. “Rory good to see you” Dean said. “You too are you alright?” Rory asked. “Oh i’m fine, just out for a walk” Dean said. “Dean what’s wrong?” Rory asked. Dean sighed, he knew nothing could get past Rory and she wasn’t going to stop until she figured what was upsetting him. “I’m having problems in my relationship” Dean said. “I heard about your divorce I’m so sorry” Rory said. Dean looked up in disbelief of course she heard about, Stars Hollow was a small town. “No I’m actually in a relationship with someone else and we had a fight about not telling anyone about our relationship” Dean said. “Would this person happen to be anyone I know” Rory asked “No no you don’t know them” Dean said. “Well what’s troubling them?” Rory said. “They feel like I’m hiding the fact of our relationship from everyone- and maybe I am, but I’m going through a divorce right now and I wanted to wait until everything was settled before I told anyone. Now I’ve made them feel like there nothing to me” Dean said. “Dean you are the most romantic person I know. Divorce can be very unsettling and hurtful for anyone going through it and it takes time before your truly ready to move on. If whoever your dating, feels like there nothing to you, then you both need to talk with each other. “Rory thank you for this talk. I needed it. By the way the person who I was talking about was...Jess” Dean said. Rory stood in shock, Jess Mariano and Dean together, her two ex boyfriends were dating. 

"Dean I- I can't believe it. I mean you and Jess.... I'm happy for both of you" Rory said. "You are?" Dean said surprised. "Of course, I'm going to be that one ex who hates to see her exes unhappy, Now go talk to Jess" Rory said. "I will, thank you for being happy about me and Jess" Dean said as he went back home


	7. Apologizes and Surprises

**Summary for the Chapter:**

> Dean has a talk with Jess about their fight

Dean heads back to the house and then he notices that the light’s are on. When he walks in the house, Jess is in the kitchen. 

“Hey” Jess says. “Hi” Dean said. “Where were you?” Jess asks. “Out for a walk” Dean says. “Oh, well when I didn’t hear from you, I got worried sick” Jess said angry. “Jess I’m sorry” Dean said. “Yeah I’m sure you are” Jess says about to leave. “Wait, don’t leave yet. At least hear me out ” Dean says grabbing Jess’s hand. “Dean-” Jess was about to say. “Please” Dean said. “All right I’m listening” Jess said. 

“You’ve helped me so much ever since my divorce. You do everything for the kids better than me, but you also love it more than…. my ex wife ever did. I think I realized her starting to distance herself away from me when I brought up having another kid. One was enough for her, but I wanted another one. Then we had our son, and she seemed happy at first, but as the kids got older I guess she wanted her own life”. Dean said with tears in his eyes.

“But you, your so much different than her Jess. You love spending time with me and my kids. Even when I don’t say it, you pick up the kids from school and help me out a lot of times. I’ve known you for a long time and I can honestly say, your really something special Jess. I was being an idiot and I’m so-” Jess interrupted Dean with a hug and a kiss on a cheek. 

“Huh you didn’t let me finish” Dean said smiling. “You didn’t have too, I accept your apologize” Jess said. “Yeah but what I was gonna say was would you like to move in with me?” Dean asked "I'd like that" Jess said smiling. 

The next day over breakfast, Dean told his kids about Jess moving in with them. "Yeah uncle Jess is staying forever!" Dean's daughter said. "This is gonna be so much.... wait Dad does mom know?" Dean's son asked. Dean thought about it, how would she react to the news that his old friend enemy was moving in with him. "I don't know how your mom will feel, but as long as you guys are happy, I'm happy" Dean said rustling his son's hair. "How would you guys like to help Jess move in his things today?" Dean asked. "Sure" the kids said. 

Dean and his kids drove over to Jess's apartment complex. Jess was outside loading up the moving truck when he saw Dean and the kids. "Hey guys glad you could make it. I've got some boxes upstairs you can bring down" Jess said. "Thanks we'll head right up" Dean said as they went inside the apartment. 

Jess's apartment was a one bedroom. He had pictures of his mom, Luke, some friends from his hometown and a few other people. Dean went inside Jess's bedroom to look for the boxes. He found them near Jess's closet and brought them to the living room. "Now kids these boxes are not heavy so you can carry down stairs, but you have to be careful and help each other OK?" Dean asked. "We will dad promise" Dean's kids said. While the kids went to the moving truck, Dean looked for more boxes when he heard Jess calling him. "Hey dean were almost done loading up the truck, where are you?" Jess said. "I'm in your room" Dean said. "What are you doing in here" Jess asked walking in the room. 

"Looking for more boxes" Dean said "Sure your not just snooping through my things?" Jess said teasing. "No, because I trust you.... and I wanted to know who those people are in the photos hanging on the wall" Dean asked. Jess laughed and said "Those are some friends I met during my travels. I'll introduce you to them one day". "Great, anyways we should probably finish packing and taking your stuff down to the truck" Dean said. After all of Jess's things were loaded onto the truck, the moving van headed to Dean's house, where Dean, Jess, and the movers moved all of the boxes into the house. 

Once the sun went down Jess, Dean, and the kids were exhausted and headed to bed. Then before he could even shut his eyes, Dean got a phone call.......from his ex wife.


	8. Hurtful words and Settlements

**Summary for the Chapter:**

> Dean and his ex wife have a fight about their marriage then Jess steps into to settle things

Dean woke up to the sound of his phone ringing. “Hello?” he said half asleep “Dean, it’s me sorry to bother you” his ex wife said. “Uh hi what’s up?” Dean asked. “I’m outside the house, I need to talk to you” his ex wife said. “Fine I’m coming” Dean said hanging up the phone. “Hey you all right?” Jess asked. “Yeah that was my ex wife, she wants to talk, sure it won’t take long” Dean said as he went downstairs and headed outside. 

His ex wife stood near the gate and she looked like she had been crying. “Hey what’s-” before Dean could finish his sentence, his ex wife slapped him across his face. “What the- ow! what was that for” Dean asked confused. “So who is it, huh. Who have you been dating?!” his ex wife said. “What are you talking about” Dean said. “I heard from your mother that your dating someone so who is it” she asked. “Why do you even care, were not together anymore” Dean said. “Look will you just tell who is it already” his ex wife said. “Fine you wanna know who I’m dating, it’s Jess” Dean said. “What” his ex wife said shocked. 

“Yeah that’s right, I’m dating Jess and I asked him to move with me” Dean said walking away from his ex. “Don’t walk away from me, when and how did this happen” his ex asked. “Right after you left, I was hurt so I went to get a drink. Jess helped me get home and took care of the kids while I was at work” Dean said. “I could have taken care of them if you let me” his ex said. “No you wouldn’t. You would have dropped them off at your parents while you were with your “boyfriend”. Dean said angry. “Dean, don’t blame me for this!” his ex yelled. 

“Why shouldn’t I. You never wanted to have another kid but you did anyway, you never wanted to live in Stars Hollow but you did, you probably never even loved me” Dean said. “I did love you, but you wanted to have this big family and then everything happened so fast that you didn’t ask what I wanted or what I thought” his ex said. “That is not true. I asked you if you wanted kids and if you wanted to move back home or stay in Stars Hollow. You know what, I'm not arguing about this I’m going to bed” Dean said giving up. “No, were going to settle this” his ex said angry. “No your not actually” Jess said. “Jess what are you doing?” Dean asked wondering why Jess was out of bed.

“Don’t worry. Look Dean has work in the morning, and he’ll be very tired if he doesn’t get any sleep. Now I know you don’t want to wake up your kids or all of Stars Hollow so if you could kindly leave please, that would be great” Jess said. “Who do you think you are, telling me what to do?" his ex said. "I'm the person who's here for Dean and your kids when you did not want too and I will continue to be person for them. Now goodnight" Jess said as he took Dean's hand and walked into the house then slammed the door. 

"Wow" Dean said. "What?" Jess asked. "Well first off that was kinda hot and I never would expected you to do that" Dean said. "Well it's really late and your welcome. Next time she comes around midnight, let me talk to her" Jess said yawning. "We should get back to bed" Dean said as he and Jess went upstairs. 

The next morning, Dean was still tired from last night, so Jess made the kids breakfast and dropped them off at school. Once Dean was awake, Jess had left him a text message. "Hey took the kids to school, thought that you could use the extra sleep" Jess texted. "Your the best, love you" Dean texted. "Your welcome" Jess texted back. 

Dean smiled as he laid in bed. His ex may have hurt him badly, but at least he had Jess, his kids, his parents, his friends, and residents of Stars Hollow to be there for him. Dean thought about what to do for Jess as a thank you for everything that he done, and then he got an idea.

**Notes for the Chapter:**

> Classes have started again this semester so i'll probably be uploading more chapters on the weekends if I have time.


	9. Making it official

**Summary for the Chapter:**

> Dean decides to make his relationship with Jess official.

Dean took the day from work to prepare for his surprise to Jess. He made Jess’s favorite foods and a movie. Jess would be home any minute and he wanted everything to be perfect. Jess came home and walked into the kitchen. 

“Hey Dean I dropped the kids off at your parents house” Jess said until he noticed the decor on the table. “Hey Jess” Dean said. “Hi uh what’s going on here?” Jess asked. “Well I wanted to surprise you with dinner and a movie” Dean said. “Unbelievable, you did all this for me” Jess said. Jess and Dean sat down and ate dinner. Jess completed Dean’s cooking and then they watched a movie. 

When the film was over, Dean had noticed that Jess had fallen asleep. He wanted to capture this moment so he took a photo. Then Dean posted the photo on Facebook, writing “I wanted everyone to know that Jess and I are dating and that he looks so peaceful and cute when he sleeps” with a heart emoji. Suddenly people were commenting and liking the picture. People were so happy that Dean made their relationship official.

Rory messaged Dean writing "Can't believe you told everyone! So proud of you". "Thanks Rory" Dean wrote back. Then he got a call from his mother. "Dean, I just saw your post on Facebook. When were you going to tell me?" she asked. "Mom I wasn't ready yet, I'm sorry" Dean said. "You tell the whole world about this but not your own mother, plus I thought you were working things with your ex" Dean's mother said. "Mom she cheated on me. I'm not even sure, she wants to co parent with me, but were trying to stay friends for the kids" Dean said. "Do you have any idea what people are going to say?" Dean's mother said. "Whatever they say, it won't change anything. Jess and I are together and your going to have to deal with that, goodbye" Dean said. Dean let Jess sleep while he went to get the kids.

"Dean it's late- what are you doing here?" Dean's mother said. "I'm here to get my kids mom" Dean said. "I thought you weren't getting them until tomorrow" his mother said. "Changed my mind" Dean said looking for the kids. "They just finished dinner, Dean please don't take the children now" his mother pleaded. "Mom don't start. Kids it's dad, come downstairs with your bags, were leaving" Dean yelled. "Hi dad" the kids said as they hugged Dean. "Hey go wait in the car while I talk to grandma" Dean said as the kids waved goodbye. "Dean please" his mother said. "Mom I don't want to have to do this, but you've made it clear that you do not like my relationship with Jess" Dean said. "Honey I want you to be happy, but Jess really" his mother asked "What's wrong with that?" Dean asked. "It doesn't seem like you two will work out" his mother said. "Mom are you serious?" Dean said. "Yes I am, Jess is a good person but he was trouble". "That was in the past mom. He's changed now" Dean said leaving the house. "You don't know that" his mother said. "Maybe I don't, but Jess is important to me. I hope you'll see that" Dean said getting in the car and driving away


	10. Summer Plans

**Summary for the Chapter:**

> Dean and Jess come up with an idea for the summer with the kids

Dean arrived back at the house with his kids in tow. He couldn’t believe his mom. Sure, Jess had been the new guy of Stars Hollow that caused trouble, but he had a life before coming to live with his Uncle Luke. His parents weren’t together, he had a complicated relationship with his dad, he didn’t even finish high school, etc. However, Jess found his calling in journalism and photography. The rivalry for Rory’s heart was in tense back when they were younger. Dean was Rory’s first love and Jess was the “bad boy” who everybody either loved or hated. At the time Dean did not like Jess, but he and Jess learned to let their love for Rory go. Or at least that’s what Dean thought.   
“Dad why did you pick us up early?” Dean’s daughter asked  
“Uh, I’ll tell you guys in the morning. Right now I want you guys in bed” Dean said  
Dean’s kids went upstairs to bed, as Jess woke up to the noise.   
“Hey why are the kids back so early?” Jess asked  
“I picked them from my mother’s, because she and I got into a fight” Dean said  
“What about?” Jess said  
“Well I posted picture of you sleeping peacefully and I officially came out plus I said that we were in a relationship” Dean said.  
“Dean that’s incredible… wait is your mother-” Jess said   
“No no she’s not homophobic. She was upset because I didn’t tell her first and she feels that I shouldn’t date you” Dean said  
Jess sat next to Dean silently for a second.   
“Please say something, I can’t tell how your feeling” Dean said wondering how Jess felt  
“Uh, well I’m a little upset that your mother does not respect our relationship, but I hope she learns to accept it” Jess said.  
“Yeah I hope so too” Dean said  
Dean and Jess headed upstairs to bed, then Jess had an idea.   
“How you and I take the kids on a trip for the summer?” Jess asked  
“Like a family road trip?” Dean said.   
“Yeah. We could go visit my mom in New York, then head to Venice Beach to visit my dad” Jess said.  
“We should probably let the kids decide though in the morning” Dean said  
“Yeah we should” Jess said as he turned off the lights and they went to sleep.

The next morning Dean and Jess made the kids some breakfast then they told the kids about their summer plans.   
“So Dean and I were thinking that all four of us could go on a road trip for the summer” Jess said  
“Really where?” Dean’s son asked  
“We were thinking about going to New York then Venice Beach to visit Jess’s family” Dean said  
“Oh my gosh that’s great when would we be going?” Dean’s daughter asked  
“Well we were thinking in July or August” Jess said  
“Let’s go in July!” Dean’s son said  
“Yeah a week after the fourth of the July” Dean’s daughter said  
“Sure we can do that” Dean said  
“Now the question is who’s going to pay for the round trip” Jess said  
“Well we could both pay, sound good to you” Dean asked  
“Yes it does” Jess said

**Notes for the Chapter:**

> This chapter took so long to finish, because my classes and assignments. Luckily the semester hasn't been to crazy to manage


	11. New  York Memories

**Summary for the Chapter:**

> Dean, Jess, and the kids head to New York to meet Jess's mother

Dean and Jess were packing up the car before the kids arrived home from school. They had been up since 9 am trying to get some snacks together for the kids to eat on the road. The kids were stressed over their school exams and they couldn’t wait to meet Jess’s family.   
“I think we have everything we need for tomorrow” Jess said  
“Are you sure, maybe we should check again?” Dean asked, worried about forgetting something.  
“Dean we have our books, movies, snacks, and our tickets for the flight. Now please stop worrying” Jess said hoping Dean would relax.   
“Yeah your right. I just hope the kids do well on their exams. I hate seeing them stress over tests” Dean said.   
“I do too but, they’ve been studying for weeks. I’m sure their fine” Jess said packing Dean on the back.   
The kids school bus arrived to the house and the kids stepped over the bus. They look exhausted.   
“Hey guys, how was school?” Dean asked  
“The exams were hard” Dean’s daughter said   
“Yeah and the teachers made us sit there until everyone was done” Dean’s son said  
“Well at least the exams were over. Now you guys have time to pack and get ready for tomorrow” Jess said  
“I can’t wait to leave! Can we pack any books or movies?” Dean’s daughter asked  
“You can pack some books because the flight will be long” Dean said   
Dean’s kids rushed upstairs to grab some books for the plane trip to New York.

The next morning Dean, Jess, and the kids left early to get to the airport to make it on time for their flight. The plane ride was long but, thankfully the kids were occupied. Now the plane arrived in New York, everyone was tired. Dean drove their rental car to a hotel for the night. 

"All right everyone, breakfast starts at 10 I want us all to get dressed and eat before we meet Jess's mother" Dean said waking up everyone.  
"Dad it's 9:30 in the morning, five more minutes please?" Dean's son asked  
"All right you can have five more minutes but, I want you to wait for Jess to get up before you come downstairs" Dean said  
Dean and his daughter headed downstairs to grab some breakfast.   
"Do you think we'll get to do some sight-seeing while were here dad?" Dean's daughter asked  
"I hope we do if we have time. What would you like to see?" Dean said  
" I wanna see everything! I want to see times square, the statue of liberty, ride on a subway train, and go shopping" Dean's daughter said  
"I'm sure we'll get to do whatever you want but, we have to know what everyone else wants to do as well" Dean said

Jess and Dean's son finally arrived downstairs and ate breakfast. Once everyone was finished eating, they all headed back upstairs to get dressed and to meet Jess's mother. Dean, Jess, and the kids rode a subway train then walked to Jess's mother Liz's house. Dean noticed that Jess seemed a little nervous when they made it to her apartment. 

"Hey are you all right?" Dean asked  
"Uh yeah. I mean this is the first time you and your kids are meeting my mother. Don't worry I've told her about you and the kids" Jess said, worried as he rang the doorbell  
"Now look who's worried. Everything will be fine Jess" Dean said squeezing Jess's hand tightly.   
"Jess what a surprise! Who is this?" Liz asked  
"Mom this is Dean and his children" Jess said  
"Oh of course. Hello everyone!" Liz said hugging dean and the kids  
"Hello Mrs. Danes, it's so nice to meet you" Dean said  
"T.J is at work right now so make yourselves conformable" Liz said  
Dean and the kids took a tour of the apartment. The living room walls had paintings hanging up and the kitchen smelled of basil and oregano. Then they went to Jess's old room. Jess had old band posters, a hole in his wall, an old picture of Rory on his nightstand, and various other pictures of his friends.   
"Wow Jess your room looks so cool!" Dean's son said  
"Who are these people in the pictures with you?" Dean's daughter asked  
"These are some of my old friends. I told them I was here in New York visiting so my mom's making dinner for everyone" Jess said  
"Oh really when did you tell them?" Dean asked  
"I texted them before I came down to breakfast this morning" Jess said, hoping dean wouldn't be mad  
"Great, can't wait to meet them" Dean said


	12. Confessions and Touring New York City

**Summary for the Chapter:**

> Jess's friends come over to Liz's house for dinner and the family takes a tour of New York City

Jess was excited that his friends were coming for dinner, but he wondered if his friends would accept his relationship with Dean. Jess’s other friends from his travels already knew but, he never told his friends from his hometown.  
“Jess are you ready for dinner?” Dean asked knocking on Jess’s bedroom door  
“Uh yeah I’m ready” Jess said hoping Dean wouldn’t notice anything wrong  
“You don’t sound so sure” Dean said   
“Well, I’ve been thinking about what my friends will say when I tell them that were dating” Jess replied  
“I’m sure they’ll be happy that you told them” Dean said  
“Maybe” Jess replied  
Jess’s mom had just finished cooking the meal and Dean’s kids were setting the dining table for dinner. Suddenly the doorbell rang.  
“Hello, how are you. Dinner will be ready in a few minutes” Liz said greeting Jess’s friends

Dean and Jess headed to the dining room to greet Jess’s friends from high schools. Nothing had changed one bit about them, though they were surprised that Dean and his kids were there.   
“Hey Jess, what’s Dean doing here?” One of his friends asked  
“Well, he’s here because-” Jess said  
“You guys are friends now. I can’t believe it”   
“Actually…. Were dating” Jess replied  
Both of Jess's friends were silent. Jess could tell they were shocked by the look on their faces. 

“Jess…. When were you gonna us!” His friends yelled as they embraced him  
Jess smiled, he was so relieved that his friends were accepting of his relationship. Dean stood there smiling as well, he knew that Jess’s friends would be accepting.   
“I was planning on telling you guys but, I wasn’t sure what you guys would think or how you would feel” Jess said  
“Jess come on man, you know we want you to be happy and find love” His friend said

Dinner went along smoothly. Jess and his friends reminisced about their high school days and talked about what they had been up to now. After dinner, Jess’s friends said their goodbyes and left. Liz and Jess were in the kitchen cleaning up while Dean and the kids were in the living room. 

“You know Jess, I’m so glad you came to visit” Liz said washing the dishes  
“Thanks Mom, it was great seeing you again” Jess replied  
“I really mean it. I’m happy that you're with someone who makes you laugh, smile, and who cares for you” Liz said  
“Yeah I mean even though Dean and I started out as rivals, we grew over the years and realized that they were something between us when we met again” Jess said

Jess, Dean, and the kids left Liz’s house that night and headed back to the hotel. Then the next morning, they all took a tour of New York City. They visited times square, the statue of liberty, and many other places. Dean’s kids took plenty of pictures. After their tour, everyone packed up their belongings and took a taxi to the airport.

“I hope you all have a safe and nice trip to California when you visit your dad” Liz said as the family were ready to board the plane  
“Thanks mom we will” Jess said  
“It was lovely to meet you, Liz” Dean said  
Liz waved goodbye as the family boarded the plane.

**Notes for the Chapter:**

> With everything going on right now, I decided to write another chapter since I have plenty of time to update this story


	13. The Question

**Summary for the Chapter:**

> Dean and Jess have been together for almost 2 years now at this point.

After their trip to New York City, Dean and Jess headed home back to Stars Hollow. Jess and the kids couldn’t wait to get home, though Dean still felt missing something in a way.

Due to the pandemic, they had to cancel the rest of their trip and soon enough the schools and businesses were closing as well. 

The kids would miss their friends deeply but they loved that they could spend more time with Dean and Jess.

Dean was feeling a little down these days and Jess began to notice it.

“Dean, everything ok?” Jess asked

“Huh, oh yeah just lost in thought” Dean said trying to seem cheerful 

“Well today, I’ll make breakfast for everybody and make sure the kids are in class on time” Jess said 

As Jess went downstairs, Dean laid in bed. He was wondered if now was the right time to propose to Jess. They were together for almost two years. Dean and Jess had talked about the idea before, but they weren’t sure if they should even go through with the idea now. 

Dean decided to take a chance and go for it. Whatever Jess’s answer was, he was going to be fine with it. 

Later that night, after the kids had eaten dinner, brushed teeth, and went to bed; Dean went to get the ring from his office. Jess was busy washing the kids when Dean called him to his office.

“Hey what’s up” Jess stopped in the doorway when he saw dean’s office, the floor was covered with roses in the shape of a heart and there candles lit on the windowsill. 

“Dean what’s going on?” Jess asked shockingly 

“Jess, when we first met we were rivals. We fought each other constantly for Rory’s affection until we grew older and realized that we just denying ourselves for each other. I want us to be happy together for a long time. I know that some people may not accept us and that’s fine as long as we are a team and we lose sight of what matters. Will you marry me?” 

Jess’s tears eyes began to tear up. He was blown away. 

“Wow I can’t believe this, I thought we were gonna wait a bit” Jess said  
“I know but I couldn’t wait anymore” Dean said

“Well then my answer is yes” Jess said

**Notes for the Chapter:**

> I was so busy with schoolwork that I barley found the time to post this


End file.
